tert-Butyl N-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)amino]-prop-yl}carbamate.

In the title compound, C(18)H(21)ClN(2)O(4), the mol-ecular sytructure is stabilized by two intra-molecular N-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers with graph-set motif R(2) (2)(10). N-H⋯O hydrogen bonds further link the dimers into C(10) chains along [010].

Related literature

For biological applications of 2-amino-1,4-naphtho­quinones, see: Kapadia et al. (2001 ▶); Brun et al. (2005 ▶); Hallak et al. (2009 ▶); Bolognesi et al. (2008 ▶). For a similar hydrogen-bonding pattern in a related compound, see: Lynch & McClenaghan (2003 ▶). For graph-set notation see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H21ClN2O4

M = 364.82

Monoclinic,

a = 5.5172 (2) Å

b = 16.6134 (6) Å

c = 19.6758 (6) Å

β = 95.709 (3)°

V = 1794.53 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.10 mm−1

T = 150 K

0.2 × 0.15 × 0.02 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.551, T max = 1

9109 measured reflections

3149 independent reflections

2620 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.07

3149 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029674/bx2415sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029674/bx2415Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029674/bx2415Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H21ClN2O4	F(000) = 768
Mr = 364.82	Dx = 1.35 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 3882 reflections
a = 5.5172 (2) Å	θ = 3.5–66.1°
b = 16.6134 (6) Å	µ = 2.10 mm−1
c = 19.6758 (6) Å	T = 150 K
β = 95.709 (3)°	Plate, red
V = 1794.53 (11) Å3	0.2 × 0.15 × 0.02 mm
Z = 4

Agilent Xcalibur Atlas Gemini ultra diffractometer	3149 independent reflections
Graphite monochromator	2620 reflections with I > 2σ(I)
Detector resolution: 10.4186 pixels mm-1	Rint = 0.040
ω scans	θmax = 66.3°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −6→6
Tmin = 0.551, Tmax = 1	k = −19→13
9109 measured reflections	l = −23→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2773P] where P = (Fo2 + 2Fc2)/3
3149 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. CrysAlisPro (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl	0.06795 (8)	0.53090 (3)	0.20487 (2)	0.02752 (14)
O2	0.2272 (2)	0.68717 (8)	0.16913 (7)	0.0334 (3)
O1	0.7377 (2)	0.46056 (8)	0.05404 (7)	0.0309 (3)
C3	0.2965 (3)	0.54959 (11)	0.15192 (8)	0.0213 (4)
C2	0.4262 (3)	0.48957 (10)	0.12418 (8)	0.0195 (4)
C9	0.6701 (3)	0.59958 (11)	0.06765 (8)	0.0215 (4)
C10	0.5346 (3)	0.65804 (11)	0.09762 (8)	0.0225 (4)
C5	0.5789 (3)	0.73898 (12)	0.08553 (9)	0.0289 (4)
H5	0.4862	0.7793	0.1053	0.035*
C8	0.8508 (3)	0.62166 (12)	0.02638 (9)	0.0254 (4)
H8	0.9433	0.5815	0.0062	0.03*
C11	0.2428 (3)	0.35866 (11)	0.16149 (9)	0.0249 (4)
H11A	0.2312	0.3057	0.1384	0.03*
H11B	0.079	0.3836	0.156	0.03*
C4	0.3413 (3)	0.63466 (11)	0.14204 (9)	0.0234 (4)
C13	0.5714 (4)	0.30943 (12)	0.25169 (10)	0.0295 (4)
H13A	0.689	0.3429	0.2293	0.035*
H13B	0.6191	0.3112	0.3015	0.035*
C1	0.6246 (3)	0.51367 (11)	0.07960 (9)	0.0220 (4)
C7	0.8947 (3)	0.70260 (12)	0.01492 (9)	0.0292 (4)
H7	1.0174	0.7181	−0.0131	0.035*
C12	0.3190 (3)	0.34600 (12)	0.23726 (9)	0.0283 (4)
H12A	0.3156	0.3985	0.261	0.034*
H12B	0.1991	0.3103	0.2563	0.034*
C6	0.7587 (4)	0.76064 (12)	0.04458 (10)	0.0321 (5)
H6	0.7891	0.816	0.0367	0.039*
O4	0.7482 (2)	0.25328 (8)	0.12831 (7)	0.0324 (3)
N2	0.5892 (3)	0.22688 (9)	0.22833 (8)	0.0296 (4)
H2	0.541	0.189	0.2536	0.036*
C15	0.6766 (3)	0.20650 (11)	0.16955 (10)	0.0251 (4)
O3	0.6717 (2)	0.12504 (8)	0.16315 (7)	0.0310 (3)
C16	0.8079 (3)	0.08385 (12)	0.11316 (10)	0.0299 (4)
C17	0.6995 (4)	0.10180 (14)	0.04103 (11)	0.0413 (5)
H17A	0.5265	0.0873	0.0362	0.062*
H17B	0.7852	0.0704	0.0087	0.062*
H17C	0.7167	0.1593	0.0316	0.062*
C18	1.0756 (4)	0.10683 (15)	0.12453 (13)	0.0450 (6)
H18A	1.0957	0.1629	0.1108	0.067*
H18B	1.1704	0.0717	0.0971	0.067*
H18C	1.1332	0.1006	0.173	0.067*
C19	0.7714 (5)	−0.00400 (13)	0.13100 (13)	0.0472 (6)
H19A	0.8367	−0.0137	0.1785	0.071*
H19B	0.857	−0.0382	0.1006	0.071*
H19C	0.5972	−0.0168	0.1255	0.071*
N1	0.4113 (3)	0.40938 (9)	0.12852 (7)	0.0242 (3)
H1	0.524	0.3858	0.1098	0.029*

	U11	U22	U33	U12	U13	U23
Cl	0.0286 (2)	0.0288 (3)	0.0266 (2)	0.00320 (18)	0.01000 (17)	0.00058 (18)
O2	0.0422 (8)	0.0250 (7)	0.0349 (7)	0.0059 (6)	0.0136 (6)	−0.0064 (6)
O1	0.0360 (7)	0.0243 (7)	0.0349 (7)	0.0038 (6)	0.0156 (6)	−0.0027 (6)
C3	0.0228 (8)	0.0245 (9)	0.0168 (8)	0.0012 (7)	0.0032 (7)	−0.0004 (7)
C2	0.0218 (8)	0.0215 (9)	0.0147 (8)	−0.0003 (7)	−0.0014 (7)	−0.0004 (7)
C9	0.0232 (8)	0.0233 (9)	0.0173 (8)	0.0001 (7)	−0.0018 (7)	0.0001 (7)
C10	0.0262 (9)	0.0238 (9)	0.0166 (8)	0.0007 (8)	−0.0024 (7)	−0.0016 (7)
C5	0.0349 (10)	0.0229 (10)	0.0280 (10)	0.0024 (8)	−0.0004 (8)	−0.0005 (8)
C8	0.0266 (9)	0.0287 (10)	0.0208 (9)	−0.0012 (8)	0.0023 (7)	0.0002 (8)
C11	0.0250 (9)	0.0222 (9)	0.0272 (10)	−0.0039 (7)	0.0017 (8)	0.0005 (8)
C4	0.0270 (9)	0.0248 (9)	0.0179 (9)	0.0015 (8)	0.0005 (7)	−0.0022 (7)
C13	0.0364 (10)	0.0259 (10)	0.0256 (10)	−0.0009 (8)	0.0006 (8)	0.0013 (8)
C1	0.0242 (8)	0.0227 (9)	0.0186 (8)	0.0017 (7)	−0.0002 (7)	−0.0009 (7)
C7	0.0313 (9)	0.0337 (11)	0.0224 (9)	−0.0064 (8)	0.0010 (8)	0.0049 (8)
C12	0.0340 (10)	0.0252 (10)	0.0264 (10)	−0.0005 (8)	0.0068 (8)	0.0020 (8)
C6	0.0416 (11)	0.0235 (10)	0.0305 (10)	−0.0047 (9)	−0.0006 (9)	0.0044 (8)
O4	0.0372 (7)	0.0274 (7)	0.0341 (7)	−0.0043 (6)	0.0112 (6)	0.0053 (6)
N2	0.0356 (8)	0.0220 (8)	0.0328 (9)	0.0004 (7)	0.0110 (7)	0.0067 (7)
C15	0.0204 (8)	0.0221 (9)	0.0327 (10)	−0.0019 (7)	0.0025 (8)	0.0039 (8)
O3	0.0333 (7)	0.0228 (7)	0.0387 (8)	−0.0013 (6)	0.0131 (6)	0.0023 (6)
C16	0.0260 (9)	0.0262 (10)	0.0380 (11)	0.0019 (8)	0.0061 (8)	0.0010 (9)
C17	0.0432 (12)	0.0420 (13)	0.0382 (12)	−0.0032 (10)	0.0027 (10)	−0.0047 (10)
C18	0.0251 (10)	0.0480 (14)	0.0619 (15)	0.0053 (10)	0.0045 (10)	0.0020 (12)
C19	0.0519 (13)	0.0284 (12)	0.0632 (16)	0.0071 (10)	0.0158 (12)	0.0029 (11)
N1	0.0282 (8)	0.0212 (8)	0.0238 (8)	0.0012 (6)	0.0061 (6)	−0.0006 (6)

Cl—C3	1.7418 (18)	C7—C6	1.386 (3)
O2—C4	1.228 (2)	C7—H7	0.95
O1—C1	1.218 (2)	C12—H12A	0.99
C3—C2	1.372 (2)	C12—H12B	0.99
C3—C4	1.451 (3)	C6—H6	0.95
C2—N1	1.338 (2)	O4—C15	1.218 (2)
C2—C1	1.523 (2)	N2—C15	1.340 (2)
C9—C10	1.392 (2)	N2—H2	0.86
C9—C8	1.396 (3)	C15—O3	1.359 (2)
C9—C1	1.472 (3)	O3—C16	1.465 (2)
C10—C5	1.391 (3)	C16—C17	1.514 (3)
C10—C4	1.496 (3)	C16—C19	1.519 (3)
C5—C6	1.386 (3)	C16—C18	1.520 (3)
C5—H5	0.95	C17—H17A	0.98
C8—C7	1.389 (3)	C17—H17B	0.98
C8—H8	0.95	C17—H17C	0.98
C11—N1	1.454 (2)	C18—H18A	0.98
C11—C12	1.523 (3)	C18—H18B	0.98
C11—H11A	0.99	C18—H18C	0.98
C11—H11B	0.99	C19—H19A	0.98
C13—N2	1.453 (2)	C19—H19B	0.98
C13—C12	1.520 (3)	C19—H19C	0.98
C13—H13A	0.99	N1—H1	0.8486
C13—H13B	0.99
C2—C3—C4	123.52 (16)	C11—C12—H12A	108.9
C2—C3—Cl	123.08 (14)	C13—C12—H12B	108.9
C4—C3—Cl	113.37 (13)	C11—C12—H12B	108.9
N1—C2—C3	131.33 (17)	H12A—C12—H12B	107.7
N1—C2—C1	110.55 (15)	C7—C6—C5	120.86 (18)
C3—C2—C1	118.12 (15)	C7—C6—H6	119.6
C10—C9—C8	120.52 (17)	C5—C6—H6	119.6
C10—C9—C1	120.11 (16)	C15—N2—C13	123.56 (16)
C8—C9—C1	119.37 (17)	C15—N2—H2	118.2
C5—C10—C9	119.41 (17)	C13—N2—H2	118.2
C5—C10—C4	119.90 (17)	O4—C15—N2	125.63 (17)
C9—C10—C4	120.70 (16)	O4—C15—O3	125.34 (18)
C6—C5—C10	119.88 (19)	N2—C15—O3	109.03 (16)
C6—C5—H5	120.1	C15—O3—C16	121.37 (15)
C10—C5—H5	120.1	O3—C16—C17	110.87 (16)
C7—C8—C9	119.66 (18)	O3—C16—C19	101.83 (16)
C7—C8—H8	120.2	C17—C16—C19	110.91 (18)
C9—C8—H8	120.2	O3—C16—C18	109.84 (16)
N1—C11—C12	112.97 (14)	C17—C16—C18	112.07 (18)
N1—C11—H11A	109	C19—C16—C18	110.86 (18)
C12—C11—H11A	109	C16—C17—H17A	109.5
N1—C11—H11B	109	C16—C17—H17B	109.5
C12—C11—H11B	109	H17A—C17—H17B	109.5
H11A—C11—H11B	107.8	C16—C17—H17C	109.5
O2—C4—C3	122.17 (16)	H17A—C17—H17C	109.5
O2—C4—C10	119.68 (16)	H17B—C17—H17C	109.5
C3—C4—C10	118.15 (16)	C16—C18—H18A	109.5
N2—C13—C12	114.05 (16)	C16—C18—H18B	109.5
N2—C13—H13A	108.7	H18A—C18—H18B	109.5
C12—C13—H13A	108.7	C16—C18—H18C	109.5
N2—C13—H13B	108.7	H18A—C18—H18C	109.5
C12—C13—H13B	108.7	H18B—C18—H18C	109.5
H13A—C13—H13B	107.6	C16—C19—H19A	109.5
O1—C1—C9	122.29 (16)	C16—C19—H19B	109.5
O1—C1—C2	118.31 (16)	H19A—C19—H19B	109.5
C9—C1—C2	119.38 (15)	C16—C19—H19C	109.5
C6—C7—C8	119.67 (18)	H19A—C19—H19C	109.5
C6—C7—H7	120.2	H19B—C19—H19C	109.5
C8—C7—H7	120.2	C2—N1—C11	130.65 (16)
C13—C12—C11	113.37 (16)	C2—N1—H1	112.3
C13—C12—H12A	108.9	C11—N1—H1	117
C4—C3—C2—N1	179.24 (17)	C10—C9—C1—C2	0.8 (2)
Cl—C3—C2—N1	1.4 (3)	C8—C9—C1—C2	−179.55 (15)
C4—C3—C2—C1	−1.2 (2)	N1—C2—C1—O1	0.8 (2)
Cl—C3—C2—C1	−178.99 (12)	C3—C2—C1—O1	−178.91 (15)
C8—C9—C10—C5	0.7 (2)	N1—C2—C1—C9	179.53 (14)
C1—C9—C10—C5	−179.67 (15)	C3—C2—C1—C9	−0.2 (2)
C8—C9—C10—C4	−179.81 (15)	C9—C8—C7—C6	0.0 (3)
C1—C9—C10—C4	−0.2 (2)	N2—C13—C12—C11	−67.5 (2)
C9—C10—C5—C6	−0.7 (3)	N1—C11—C12—C13	−57.5 (2)
C4—C10—C5—C6	179.74 (16)	C8—C7—C6—C5	−0.1 (3)
C10—C9—C8—C7	−0.3 (2)	C10—C5—C6—C7	0.4 (3)
C1—C9—C8—C7	−179.97 (15)	C12—C13—N2—C15	98.8 (2)
C2—C3—C4—O2	−177.80 (16)	C13—N2—C15—O4	−1.0 (3)
Cl—C3—C4—O2	0.2 (2)	C13—N2—C15—O3	179.19 (15)
C2—C3—C4—C10	1.8 (2)	O4—C15—O3—C16	15.1 (3)
Cl—C3—C4—C10	179.81 (12)	N2—C15—O3—C16	−165.12 (15)
C5—C10—C4—O2	−2.0 (2)	C15—O3—C16—C17	−68.5 (2)
C9—C10—C4—O2	178.51 (15)	C15—O3—C16—C19	173.46 (16)
C5—C10—C4—C3	178.43 (15)	C15—O3—C16—C18	55.9 (2)
C9—C10—C4—C3	−1.1 (2)	C3—C2—N1—C11	3.6 (3)
C10—C9—C1—O1	179.49 (16)	C1—C2—N1—C11	−175.99 (15)
C8—C9—C1—O1	−0.9 (2)	C12—C11—N1—C2	−84.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.85	2.53	3.191 (2)	135
N1—H1···O1	0.85	2.1	2.576 (2)	115
N2—H2···O2i	0.86	2.22	2.873 (2)	132
C8—H8···O1ii	0.95	2.33	3.200 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.85	2.53	3.191 (2)	135
N1—H1⋯O1	0.85	2.1	2.576 (2)	115
N2—H2⋯O2i	0.86	2.22	2.873 (2)	132
C8—H8⋯O1ii	0.95	2.33	3.200 (2)	153

Symmetry codes: (i) ; (ii) .